2-Aminothiazole → 2,2,3,3-tetramethyl-N-1,3-thiazol-2-ylcyclopropanecarboxamide

HRID 1037824

反応式

HRID 1037824 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH3:7][C:8]1([CH3:16])[C:10]([CH3:12])([CH3:11])[CH:9]1[C:13](Cl)=[O:14].C(N(CC)CC)C>C(Cl)Cl.C(Cl)(Cl)Cl.O>[CH3:7][C:8]1([CH3:16])[C:10]([CH3:12])([CH3:11])[CH:9]1[C:13]([NH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1)=[O:14]

参加物

7

反応物 3

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chloride

生成物 1

HCID 7224802,2,3,3-tetramethyl-N-1,3-thiazol-2-ylcyclopropanecarboxamide収率 14%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
35 °C

実験手順

To a solution of 2-aminothiazole (0.39 g, 3.9 mmol) in 10 mL of methylene chloride at 0° C. was added a solution of the product from Example 1A in 8 mL of chloroform, followed by triethylamine (1.0 mL, 7.7 mmol). The mixture was stirred for 7 hours at 35° C., cooled to ambient temperature and diluted with water. The phases were separated and the aqueous phase was extracted with methylene chloride. The combined organic extracts were washed twice with water and then brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by column chromatography (SiO2, 30-60% ethyl acetate/hexanes gradient) afforded 0.11 g (14%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 1.18 (s, 1H), 1.25 (s, 6H), 1.35 (s, 6H), 6.92 (d, J=3.4 Hz, 1H), 7.39 (d, J=3.4 Hz, 1H), 10.7 (s, 1H); MS (DCI/NH3) m/z 225 (M+H)+. Anal. Calculated for C11H16N2OS: C, 58.90; H, 7.19; N, 12.49. Found: C, 59.03; H, 7.34; N, 12.34.

後処理

  1. temperaturecooled to ambient temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with methylene chloride
  4. washThe combined organic extracts were washed twice with water
  5. dry with materialbrine, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by column chromatography (SiO2, 30-60% ethyl acetate/hexanes gradient)

出典と根拠

ORDレコード
ord-d02d9507dea14d3e9cc767ebc52bba58
出典データセット
uspto-grants-2013_10
特許番号
US08546583B2

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